For example, last year I was looking at Bogota, Colombia to LON. This was quite pricey, but it turned out if I bought separate tickets - Bogota to Orlando, Florida, and then an Air Berlin flight to London was pretty well priced.

Even better, I checked and it went via Dusseldorf. However if I just bought the leg to Dusseldorf, caught the 20 min train to Cologne and flew from there, it got cheaper still.

This of course requires hours of messing around with flight websites, and often knowledge (like that Dusseldorf and Cologne are close by). Surely there's a simpler way?

Eg, I'm looking at flights from Vancouver to Bangkok, and also from LON to either SCL or EZE or Lima or Quito. One to Quito goes to the Netherlands, somewhere in the Antilles islands, onwards to Guayaquil in Ecuador and then to Quito. 4 flights requires all sorts of playing to find the cheap legs, if any. Surely there's a 'cheapest paths' search engine that can take care of this somehow, or a simpler way?

The thing is, it's something that some app could totally do. I can do it manually, it just takes forever, with kayak.co.uk and google maps open for hours ;)
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Mark MayoSep 21 '11 at 15:18

Could you mention ballpark figures of cost differences you found between results thrown up by travel sites vs what you found via manual searches? That will give a sense of whether any other site I come across matches savings.
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Ankur Banerjee♦Sep 21 '11 at 15:30

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For example, with a walk-in at Flight Center, LON to Vancouver one-way (or return if it's cheaper), plus a return from Vancouver to Bangkok, I was quoted 1408 pounds. With two searches on Kayak, I got that down to 800 quid. After searching through some more specials websites and airlines themselves, it's down to around 550 (one-way to Vancouver + return to Bangkok).
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Mark MayoSep 21 '11 at 16:10

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Specifically for the BKK flight, it may be good to look up AirAsia fares to some of the cities which are somewhat closer to Vancouver (e.g. HKG, CAN, ICN, KIX), and then find a fare to there (on Kayak, ITA Matrix).
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dbkkSep 23 '11 at 9:31

2 Answers
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For multi-city trips, unfortunately, I don't think an 'optimized' search engine exists, and the sites like Kayak, mostly route using a single network of airlines, which may or may not be the cheapest option.
You do have to spend time and be a bit creative in charting itineraries. Here's a protocol that has worked well for me -

Chart out the major cities in your itinerary, and work out the most efficient routes connecting them. The trick here is to factor in as many round trips as your time permits - needless to say, round trips are significantly cheaper than one-way options. You may have to find a central destination, and establish that as a hub - a well-connected airport with an international airline hub will serve well.

For the smaller cities, look up regional, low-cost airlines (the likes of Vueling, Southwest, etc.).

Finally, connect all the dots.

This requires effort, but in essence, follows that same 'hub' concept that has existed, in the US at least, for many decades.

Still not entirely what I'm after as it wasn't the 'Holy Grail' but it's pretty good, and is basically the pattern I followed today to find a flight from Vancouver to CHC. Also found a bug in kayak.com software while I was at it(!). Anyway, I'll give you the bounty but leave the question open for a while to see if I get anything else ;)
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Mark MayoOct 1 '11 at 9:09

Thanks! My itinerary was from the US - Spain, returning from Italy, back to the US. And I 'hubbed' at Spain (BCN). Saved a boatload, as compared to the obvious US - Spain - Italy - US route. Only caveat - a night at the airport :)
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rs79Oct 3 '11 at 13:14

Expedia and lastminute flight searches will show you flights with stops. It also shows the Cheapest flights with 0, 1 or 2+ stops for you to compare.

While it might not be as cheap as booking all the flights individually yourself (it seems fairly cheap £610 from vancouver to bangkok next month), expedia does make sure your carriers are in the same airline group, meaning that if your first flight is late and you miss your connecting flight, your carrier will get you on another one. If you book your flights individually, you will not get this protection (you can claim on your travel insurance, but i'm sure there will be an excess)

Also if you buy each ticket individually you probably have to go through immigration and re-check in at each stop.

Having bought tickets individually in the past, I can confirm you don't as a passenger have to re-enter through immigration (apart from the US). However the trick is that your baggage might exit, meaning if you want it you'll need permission (visa) to get out. Or do what I did and beg a Kazakhstan official to exit for me and find my bag, she was very kind :)
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Mark MayoOct 1 '11 at 9:07